Bob Dresses for Halloween

by LaffWithMe

Caution: This Sex Story contains strong sexual content, including Ma/Ma, Consensual, CrossDressing, True Story, First, Oral Sex, Size, .

Desc: Sex Story: With his wife's blessing and encouragement Bob ventures out on his first cross-dressing foray. Let us say he is deeply impacted by the experience.

© 1995, 1999 LaffWithMe Press

The following material is protected under the copyright laws of the United States of America. This work may not be distributed for profit, in any form, without the written permission of the author or his agent.

Bob was trembling as he walked through the women's section of the large department store. There were very few people in the store this morning, yet he was certain that each of them was watching him. Seeing his wife should have calmed him but it didn't.

"See, Bob, I told you the floor would be empty this morning. Come back to the fitting rooms, I think I've got some great outfits for you to look at."

"Jesus Casey, I don't know if this is really going to work. Maybe we should forget it." Bob replied.

"Oh no, you're not going to chicken out on me now." Casey grabbed his arm and pulled him through the curtain, then into a small cubicle. "You said you wanted to do it and I think it's a turn-on. Anyway, you'll never know if you like it until you actually try it. And what better time than Halloween?"

The 'it' in question was something that had haunted Bob since he was a teenager, maybe even before that. The 'it' was his fascination with women's clothing - no, not a fascination, a desire to dress in women's clothing. It was more than just dressing the part; he knew down deep, that he wanted to experience being a woman.

"Now strip while I go get your new wardrobe". At this point it seemed that Casey was more excited about this adventure than Bob. As the cubicle door swung closed, Bob stripped to his nylon bikini shorts. He watched himself in the mirror as each piece of clothing was removed. Then, almost naked, he examined himself more closely, trying to imagine how he would look in... Shit, he had a hard time even thinking of the word... 'drag'.

Still, he did think he had a nice body, for a man or a woman. His five foot eight inch frame was lean and firm. He had continued to swim and run marathons, the sports that had gotten him small scholarships in college. His rich brown eyes made a nice contrast to his fair Nordic skin and collar length blond hair. His nose was very straight; it almost seemed to be a pointer to his lips that were slightly large and full in appearance. He shrugged his shoulders, flexed his muscles slightly, and noticed his nipples move as he did so. He absent-mindedly pinched one and brought it to erection. His nipples were almost as large as Casey's were and very sensitive. His bikini shorts were snug and he could clearly see the outline of his cock and balls. Turning to view his profile, he decided that he had a nice ass atop his well-shaped legs.

Casey was suddenly back with an armload of clothing. "Preening?" she said. "Here, start with these panty hose, but don't get attached to them. I think some nice patterned nylons will look better.

Bob opened the package and removed the pantyhose, pausing to feel the texture. Casey watched and smiled. As Bob slipped on the stockings he saw the look in Casey's eyes. That same look when she had caught him trying on her pantyhose a few weeks before. He had been embarrassed and ashamed when she walked in, fully expecting her to be furious. Instead she had a devilish look in her eye and a clearly mischievous grin on her face. Bob had known early in their relationship that Casey enjoyed some unusual sexual activities. In fact, when he met her, he thought she was gay. Thus it was no real surprise when she was the one to suggest that he dress for Halloween.

Casey knelt in front of Bob and smoothed the stockings from ankle to thigh. The feel of her hands sliding over the nylon on his legs, the press of the panty top against his cock caused his cock to swell. Casey looked at the sharp outline of the hard cock bulging against the thin shorts and sheer pantyhose. She could clearly see the balls separated by the seam of the stockings, the shaft pressed to the side, the flair of the cock head.

She pressed her face to the knob and kissed it lightly. "Well sweetheart, I see we're going to have a problem hiding this little monster" she laughed. Not that Bob had a monster. On the contrary it was probably slightly small, but in Casey's view was perfectly shaped. The shaft was very straight with a prominent blue vein down the side. Casey loved feeling this vein bulge and pulse as her tongue caressed it. The shaft was crowned with a large head that looked like some kind of helmet. What Casey enjoyed most was the fact that this cock would get extremely hard. When Bob got aroused his cock truly felt like a bone wrapped in warm skin.

"Casey, I don't think we should do anything here. Let me just try on the clothes before anyone comes in." Bob knew that his wife loved sex just about every way except in the bedroom with the lights off. Despite his hard cock he didn't want to be fucking in the women's fitting room of the biggest store in town.

Casey rubbed her cheek against the solid bulge. "But sweetheart, you can't try on clothes with this big cock sticking out. It'll ruin the line." She was hooking her fingers into his briefs, pulling down the panty hose and briefs together. In a second his cock sprung free of the confinement.

Casey talked to the cock swaying in front of her nose. "Oh poor baby, you're so pale and white. Hasn't daddy let you play out in the sun? Let mommy kiss that pretty pink head of yours."

She grabbed the shaft, brought it to her lips and began kissing the end. She held the tip to her lips and french kissed it several times, licking the point of her tongue into the hole. She soon was rewarded with drops of precum oozing out to meet her tongue. She tightened her grip on the bone; watched the head turn a darker shade as she squeezed the blood engorged shaft. The blue vein swelled and she licked it then sucked the cock into her mouth.

Bob groaned and gave up to the pleasure. He held her head and began pumping his cock into her mouth as she expertly sucked and tongued the shaft. Her hand worked the shaft back and forth, jacking him off into her mouth. She reached down, pushed her hand beneath her waistband and began finger fucking herself in time to the cock fucking her mouth. Bob could hear voices in the distance but it was too late to stop. He felt his juices begin to boil. He moaned and fucked her face harder. Casey let her tongue work its magic and quickly brought Bob to a climax. She felt his cock pulse in her hand; she sucked and drank as the cum spurt into her mouth. She rubbed her own clit rapidly, achieving a small orgasm for herself.

"Now, don't you feel better?" she said as she stuffed his now limp cock back into his briefs, then pulled them up along with the pantyhose.

Casey stood, retrieved a lacy black bra, which she slipped onto him. Bob shivered with excitement as she snapped the bra in place. The bra had padding in the cups and he could feel the structure of the bra pushing against his pectorals. "I was thinking of going for bigger boobs," he said, as he looked down at the small cups.

"Oh shit, you guys and your tit mania! Look, big tits will look really fake on you. Look in the mirror, this thing actually gives you a little bit of cleavage."

Bob turned to the mirror and leaned forward slightly, amazed at how sexy he felt in bra and panty hose. Marveling that indeed this bra managed to push his chest enough to give a hint of rounded flesh.

"Here you go, baby, you're going to like this." Casey pulled a black sheath from behind some other dresses. "Slip this on."

Bob wiggled into the dress, feeling it cling to his body. He felt as if he was wrapped in black SaranWrap. The dress fit perfectly. It had a long slit up one side; no sleeves, a high neck and a heart shaped opening in the bodice. The point of the heart accentuated the newly formed little tits that the bra forced up.

"Here. Step into these shoes." Casey slid a pair of low heeled, black, open shoes onto his feet. "Move around a little bit now. Let's see how this is going to work."

Bob stepped haltingly back and forth in front of the mirror. Wobbling on the low heels, he looked rather ungainly yet he was clearly going to be striking in this outfit. He moved his leg and watched as the slit on the dress opened to reveal skin almost to his ass. "Goddam baby. You do have a pair of legs! Let's see how that ass looks." Casey turned him to view a profile. His ass bulged out seductively; his chest had a nice curve as if he really had firm small breasts. His cock was again throbbing and pushed out at the material! "Oh shit, sweetheart. We just have to do something about that cock of yours. We'll have to try some tummy tuck panties, maybe the elastic will be enough to contain you."

All in all, even without makeup, Bob had become a very sexy looking girl. He could hardly contain his excitement.

"Let's try on a couple of these other dresses, but I think that one is going to be the best", Casey said.

Reluctantly, he removed the dress and tried on the others that she had brought him. However, nothing could top the sheath with the slit up the side.

In the days that followed, Bob practiced walking in his new heels. He insisted on wearing his new outfit every night, to the point that Casey had to stop him lest he wear it out before the big night.

She taught him how to sit, how to walk. She tried to teach him how to dance. This turned out to be the second most difficult part of the transition. They made some progress but decided not to worry about it. They would be together and would only be dancing with each other so they figured no one would notice who was leading whom.

.... There is more of this story ...

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Story tagged with:
Ma/Ma / Consensual / CrossDressing / True Story / First / Oral Sex / Size /